Distannylated Bithiophene Imide: Enabling High‐Performance n‐Type Polymer Semiconductors with an Acceptor–Acceptor Backbone

Shi, Yongqiang; Guo, Han; Huang, Jiachen; Zhang, Xianhe; Wu, Ziang; Yang, Kun; Zhang, Yujie; Feng, Kui; Woo, Han Young; Ortiz, Rocío Ponce; Zhou, Ming; Guo, Xugang

doi:10.1002/ange.202002292

Cited by 26 publications

(13 citation statements)

References 65 publications

(40 reference statements)

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“…However, the number of high‐performance A–A‐type polymers, especially, for all‐PSCs is very limited. [ 32 ]…”

Section: Figurementioning

confidence: 99%

“…As shown in Scheme S1 (Supporting Information), Y5‐Br was copolymerized with recently developed BTI‐Tin [ 32 ] to afford a novel A–A‐type polymer acceptor L14. To show the effect of narrow‐ E g polymer with A–A‐type backbone on promoting all‐PSC performance, a D–A‐type analog polymer L11 was also synthesized for comparison.…”

Section: Figurementioning

confidence: 99%

“…We understand that the measurements on the energetic levels are subject to experimental errors, and hence are not supposed to count on the exact values. However, by replacing the thiophene in L11 with BTI in L14, we are confident that the energetic levels of L14 are downshifted compared with those of L11, [ 32,49 ] resulting in a larger energetic offset in PM6:L14. There are several possibilities for the absence of the redshift of below‐gap absorption in PM6:L14.…”

Section: Figurementioning

confidence: 99%

“…However, the number of high-performance A-A-type polymers, especially, for all-PSCs is very limited. [32] Inspired by the great success of FREA polymerization for increasing the absorption of all-PSCs and the A-A strategy for improving the electron transport property of n-type polymers, herein we combine above two strategies to design and synthesize a new narrow-E g polymer acceptor L14 (Figure 1a) by copolymerizing the recently developed distannylated BTI (BTI-Tin) [32] with brominated FREA Y5 (Y5-Br). [29] As expected, polymer L14 maintains the promising features of the corresponding FREA moiety, e.g., a broad absorption in the range of 600-900 nm with a narrow E g of ≈1.39 eV and a high absorption coefficient of 1.44 × 10 5 cm −1 .…”

mentioning

confidence: 99%

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A Narrow‐Bandgap n‐Type Polymer with an Acceptor–Acceptor Backbone Enabling Efficient All‐Polymer Solar Cells

et al. 2020

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of these FREAs can be fine-tuned by optimizing the intramolecular charge transfer character while maintaining their key characteristics as efficient electron acceptor materials. [4-6] The FREAs with fine-tailored properties enable the state-of-the-art power conversion efficiencies (PCEs) surpassing 16% in OSCs. [7-12] Among various OSCs, all-polymer solar cells (all-PSCs) employing conjugated polymers as both the electron donors and acceptors, have recently attracted great attention because of some unique advantages including superior stability and mechanical robustness. [13-20] However, only a few polymer acceptors can yield PCEs over 8% till now (see Figure S1 and Table S1, Supporting Information) due to the scarcity of highly electron-deficient building blocks. For instance, classical naphthalene diimide and perylene diimidebased donor-acceptor (D-A)-type polymer acceptors (see Figure S2a, Supporting Information) suffer from poor absorption coefficient in the long-wavelength region and (or) the localized lowest unoccupied molecular orbital (LUMO), which limits the short-circuit currents density (J sc) and V oc , together with Narrow-bandgap polymer semiconductors are essential for advancing the development of organic solar cells. Here, a new narrow-bandgap polymer acceptor L14, featuring an acceptor-acceptor (A-A) type backbone, is synthesized by copolymerizing a dibrominated fused-ring electron acceptor (FREA) with distannylated bithiophene imide. Combining the advantages of both the FREA and the A-A polymer, L14 not only shows a narrow bandgap and high absorption coefficient, but also low-lying frontier molecular orbital (FMO) levels. Such FMO levels yield improved electron transfer character, but unexpectedly, without sacrificing open-circuit voltage (V oc), which is attributed to a small nonradiative recombination loss (E loss,nr) of 0.22 eV. Benefiting from the improved photocurrent along with the high fill factor and V oc , an excellent efficiency of 14.3% is achieved, which is among the highest values for all-polymer solar cells (all-PSCs). The results demonstrate the superiority of narrow-bandgap A-A type polymers for improving all-PSC performance and pave a way toward developing high-performance polymer acceptors for all-PSCs.

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“…However, the number of high‐performance A–A‐type polymers, especially, for all‐PSCs is very limited. [ 32 ]…”

Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

mentioning

confidence: 99%

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A Narrow‐Bandgap n‐Type Polymer with an Acceptor–Acceptor Backbone Enabling Efficient All‐Polymer Solar Cells

et al. 2020

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“…The M n of the P346-based polymer obtained using a microwave reactor and by conducting the Stille coupling reaction using BTI-Sn and BTI-Br monomers was high (35.5 kDa). 148,149 The electron mobility recorded for the high-molecularweight P346 was higher (2.60 cm 2 V À1 s À1 ) than that of the low-molecular weight polymer. On the other hand, the BTI-based polymer P351 synthesized using the acceptor-acceptor (A-A) strategy (to obtain unipolar ntype characteristics) exhibited an electron mobility of 1.23 cm 2 V À1 s À1 and a high-I on /I off ratio of 10 6 .…”

Section: Bti-derived Polymersmentioning

confidence: 97%

Recent progress in lactam‐based polymer semiconductors for organic electronic devices

Park

Lim

et al. 2021

Journal of Polymer Science

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Numerous polymer semiconductor materials with alternating electron donorelectron acceptor (D-A) structures have attracted immense attention because they exhibit excellent semiconductor performance and solution processability. These materials can be used for the fabrication of various lightweight and flexible electronic devices. In this review, we provide a brief overview of the structural features and important properties of lactams whose performance can be enhanced by introducing an acceptor in the design of D-A-type polymer semiconductor materials. The focus is on polymer semiconductor materials with lactams in their structures, such as diketopyrrolo[3,4-c]pyrrole, naphthalene diimide, isoindigo, 2,2-bithiophene-3,3-dicarboximide, and thieno[3,4-c]pyrrole-4,6-dione. The recent advances made in the field in the last 3 years are discussed. In addition, the application of polymers for the fabrication of organic electronic devices and the progress in the field are discussed.

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One‐Step Sixfold Cyanation of Benzothiadiazole Acceptor Units for Air‐Stable High‐Performance n‐Type Organic Field‐Effect Transistors

et al. 2021

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Reported here is a new high electron affinity acceptor end group for organic semiconductors, 2,1,3‐benzothiadiazole‐4,5,6‐tricarbonitrile (TCNBT). An n‐type organic semiconductor with an indacenodithiophene (IDT) core and TCNBT end groups was synthesized by a sixfold nucleophilic substitution with cyanide on a fluorinated precursor, itself prepared by a direct arylation approach. This one‐step chemical modification significantly impacted the molecular properties: the fluorinated precursor, TFBT IDT, a poor ambipolar semiconductor, was converted into TCNBT IDT, a good n‐type semiconductor. The electron‐deficient end group TCNBT dramatically decreased the energy of the highest occupied and lowest unoccupied molecular orbitals (HOMO/LUMO) compared to the fluorinated analogue and improved the molecular orientation when utilized in n‐type organic field‐effect transistors (OFETs). Solution‐processed OFETs based on TCNBT IDT exhibited a charge‐carrier mobility of up to μe≈0.15 cm2 V−1 s−1 with excellent ambient stability for 100 hours, highlighting the benefits of the cyanated end group and the synthetic approach.

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Distannylated Bithiophene Imide: Enabling High‐Performance n‐Type Polymer Semiconductors with an Acceptor–Acceptor Backbone

Cited by 26 publications

References 65 publications

A Narrow‐Bandgap n‐Type Polymer with an Acceptor–Acceptor Backbone Enabling Efficient All‐Polymer Solar Cells

A Narrow‐Bandgap n‐Type Polymer with an Acceptor–Acceptor Backbone Enabling Efficient All‐Polymer Solar Cells

Recent progress in lactam‐based polymer semiconductors for organic electronic devices

One‐Step Sixfold Cyanation of Benzothiadiazole Acceptor Units for Air‐Stable High‐Performance n‐Type Organic Field‐Effect Transistors

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